1,4-Dioxane → 1-Bromo-5-isocyanatopentane

HRID 1003740Notes

Reaction equation

HRID 1003740 reaction equation
C[Si]([N:5]=[N+]=[N-])(C)C.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]C(Cl)=O.[O:17]1[CH2:22]COCC1>>[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:5]=[C:22]=[O:17]

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 78378AzidotrimethylsilaneHCID 898486-Bromohexanoyl chloride

Product 1

HCID 144828831-Bromo-5-isocyanatopentaneYield 78%

Conditions

Temperature
80 °C

Procedure

To a solution of trimethylsilylazide (7.46 mL, 93.67 mmol) in dioxane (10 mL), 6-bromohexanoyl chloride (10 g, 46.83 mmol) was added and the solution was heated at 80° C. for 4 hours. The reaction mixture was concentrated to give a liquid. Distillation (oil bath temp. 135° C., distilling temperature 94° C.) of the liquid yielded 7 g (78%) of the product as a liquid: 1H-NMR (CDCl3) δ1.50-1.92 (m, 6 H), 3.33 (t, J=7.0 Hz, 2H), 3.43 (t, J=7.0 Hz, 2H). IR: 2360 cm-1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a liquid
  3. distillationDistillation (oil bath temp. 135° C., distilling temperature 94° C.) of the liquid

Sources & evidence

ORD record
ord-5e849550696f4bfe949da7be68684883
Source dataset
uspto-grants-2000_04
Patent number
US06046331

Reaction notes

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